Benzoyl chloride → HCID 68065509, compound

HRID 2044071Notes

Reaction equation

HRID 2044071 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[O:28])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[C:11]([C:37](=[O:39])[NH2:38])=[CH:10][CH:9]=2)[CH2:3]1.CCN(CC)CC.[C:47](Cl)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1COCC1>[C:47]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[O:28])[CH2:23][CH2:22]4)=[CH:19][CH:20]=3)[C:11]([C:37](=[O:39])[NH2:38])=[CH:10][CH:9]=2)[CH2:3]1)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68051772HCID 68051772, compound

Product 1

HCID 68065509HCID 68065509, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (R)-benzyl 4-(4-(6-(3-aminopiperidin-1-yl)-3-carbamoylpyridin-2-ylamino)phenyl)piperazine-1-carboxylate (1.1 g, 2.077 mmol) and Et3N (0.579 mL, 4.15 mmol) in THF (10 mL) was added benzoyl chloride (0.350 g, 2.492 mmol). The reaction mixture was stirred at rt for 30 min., quenched with satd NaHCO3, and extracted twice with CH2Cl2. The combined organic layers were concentrated and the residue was triturated with CH2Cl2 to obtain 1.15 g of (R)-benzyl 4-(4-(6-(3-benzamidopiperidin-1-yl)-3-carbamoylpyridin-2-ylamino)phenyl)piperazine-1-carboxylate as an off-white solid. LCMS: (M+H)+=634.40. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.08 (1H, s), 8.30 (1H, d, J=8.06 Hz), 7.67-7.96 (3H, m), 7.30-7.37 (3H, m), 7.19-7.30 (7H, m), 6.59 (2H, d, J=9.15 Hz), 6.06 (1H, d, J=9.15 Hz), 4.98 (2H, s), 4.34-4.58 (1H, m), 3.93-4.10 (1H, m), 3.75-3.91 (1H, m), 3.08-3.36 (8H, m), 2.52-2.90 (1H, m), 1.86 (1H, s), 1.59-1.75 (1H, m), 1.47-1.58 (1H, m), 1.40 (1H, d, J=2.93 Hz).

Workup

  1. customquenched with satd NaHCO3
  2. extractionextracted twice with CH2Cl2
  3. concentrationThe combined organic layers were concentrated
  4. customthe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-2386654dbde24c13b3644a502aaa194e
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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